Regiospecific Synthesis of Tetra-Substituted Furans

Leiv K. Sydnes, Rustem Isanov, Myagmarsuren Sengee, Francesco Livi

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α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.
Original languageEnglish
JournalSynthetic Communications
Issue number21
Pages (from-to)2898-2905
Publication statusPublished - 2013
Externally publishedYes

Bibliographical note

Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.


  • Conjugated acetylenic ketones
  • Ketoesters
  • Propargylic alcohols

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